10 Best Boy with a Hat Paintings

The Torn Hat Thomas Sully

The word “best” in this title is, of course, subjective. What this gallery of a post features are some of my favorite boy with a hat paintings from the 18th to the 20th centuries.

Boys wearing hats are an interesting subject in painting. They wear on their faces the innocence of their young age, but mingled with it are other feelings or moods, not all of them straightforward.

Not all of these paintings are what you would call cute: take the boy with a hatchet, for example.

To some extent, these paintings chart hat styles through the ages. Not two of the hats are quite alike, are they?

Let’s not forget that not so long ago, hats were about as ubiquitous as sports caps are today, and decidedly more stylish…

What do you make of these paintings? Is there any one in particular you like?

5 thoughts on “10 Best Boy with a Hat Paintings

  1. The torn hat is undoubtedly my favorite. Mostly because my grandmother recreated this piece in an early art lesson and I grew up seeing it… while it was different from the classic, the essence was there. The unexpected light in what should be a dark shadow of his face makes it interesting to me and he has an adventurous spirit. I can tell

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